


Anything for Sammy

by Anonymous



Category: Supernatural
Genre: Anxiety, Dean Winchester is Sam Winchester's Parent, Desperation, Drunk Sex, First Time Bottoming, John Winchester Being an Asshole, M/M, Outdoor Sex, Painful Sex, Pre-Canon, Prostitution, Rough Oral Sex, Rough Sex, Spit As Lube, Stranger Sex, Underage Drinking, Young Dean Winchester, Young Sam Winchester
Language: English
Status: Completed
Published: 2020-11-13
Updated: 2020-11-13
Packaged: 2021-03-10 01:55:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,238
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27536395
Author URL: https://archiveofourown.org/
Summary: John is gone, and he won't be back anytime soon. The boys are running out of money, so Dean does what he has to. Pre-series
Relationships: Dean Winchester & Sam Winchester
Comments: 2
Kudos: 63
Collections: Anonymous





	Anything for Sammy

**Author's Note:**

> I posted this a few years ago, deleted it, then just found it again in my docs so I'm reposting. Enjoy :) I am not caught up in the series so please don't spoil in comments

40 bucks. That’s all that was left. 40 God damn dollars, and they hadn’t heard from John in 2 weeks.

Dean ran a nervous hand through his hair, staring down at the crumpled pile of bills sitting on the kitchen table in their temporary home, trying to push down the nausea rising in his belly. 

As if on cue, Dean’s phone rang once, stopped, then started ringing again. Dean picked up immediately, ready to cry with relief that his dad was finally calling.

“Hi Dad, when are you coming back? Because we-“ Dean began hastily, but John interrupted.

“Dean, listen to me. I’m going to be longer than I thought. This nest of vamps turned out to be a bigger challenge than I planned, and I had to call in for back up. Another week, at most,” John finished, sounding clearly rushed and out of breath.

Dean’s heart dropped to his boots. “Dad…we don’t have enough money,” he said quietly, as if trying to keep it a secret.

“Dean, I gave you plenty of money. What have you been blowing it on this time? You know, you need to learn to be more responsible. How are you supposed to take care of Sam if you can’t even take care of yourself?”

“But Dad-“

“I don’t want to hear it Dean. I gave you plenty of money. You shouldn’t have blown it on useless shit.”

“But I didn’t-“

“Dean,” John barked sternly, and Dean shut his mouth. “How much do you have left?”

“40 dollars.”

Dean heard John sigh, frustrated.

“Well, figure it out Dean. Be more responsible next time. I guess you boys will just have to eat ramen noodles and saltines for the next week.”

“Yes sir,” Dean gritted out, jaw clenched in frustration.

“See you in a week, son. Take care of your brother, make sure he’s training and doing his schoolwork. You know the drill.”

“Yes sir.”

When John hung up, Dean threw his phone with too much force against the back of the couch. It bounced off and hit the wood floor with a deafening clatter, but he barely even flinched.

He hadn’t wasted the money! He honestly hadn’t. There were a lot of little things that all added up and just…before he knew it, the money had dwindled down to a measly 40 dollars.

But in his defense, he  _ was _ taking care of Sammy. Sam wanted Cheerios instead of store brand cereal, so he bought them. Sam asked Dean to get him fresh vegetables, and even though they were a little pricey, Dean did it. But what had killed them financially was Sam’s boots. While they were training, he tripped, and his already tattered and worn out boots practically fell apart. Dean couldn’t duct tape them like he had the last time that the sole of Sam’s boot fell off, and Sam had no other shoes, so Dean was forced to get him some boots.

He even went to the Salvation Army to get them, but the cheapest ones were still 20 bucks. Dean knew it was too much, and he shouldn’t have purchased them, but the look of appreciation on Sammy’s face was worth it.

So there he was, down to 40 dollars with an impossible week (and probably longer, knowing John) ahead. 

He was snapped out of his thoughts when Sam opened the front door, tossing his backpack on the floor and immediately running to the fridge for a snack.

“Hey Dean,” he said with a smile while grabbing a pudding cup from the fridge and closing the door with his foot. He walked to sit at the table across from his brother, and that was when he noticed the unmistakable stress lines on Dean’s face and the glint of worry in his green eyes.

“What’s wrong Dean?” he asked, pulling the top off of the pudding cup and licking it clean.

Dean hesitated. He knew Sam didn’t have to know about their financial struggles, which would only worry him. Sammy was only 13, and 13 year olds don’t need to hear about things like money.

“Dad isn’t going to be back for another week,” Dean admitted, absently toying with the chipped finish on the wood table.

Sam’s eyes lit up and he tried to hide it by looking down and pretending to be very interested in his pudding cup, but Dean caught it.

“You seem pretty happy about that,” he snapped with unnecessary anger.

Sam looked guilty, his puppy-dog eyes glistening up at Dean. “I’m sorry, Dean. I know you’re probably worried and everything, but…but this means that I get to actually go on a field trip. It's next Monday, and I didn’t think I was gonna be able to go because Dad would be back. I’ve never been to an aquarium before,” Sam finished, unable to keep the excitement out of his voice.

Despite his worries, Dean smiled to himself. “An aquarium? Nerd. Well, I hope you have fun Sammy, I’ve never been to one either. Although looking at a bunch of fish and listening to a tour guide explain a ton of boring crap about them isn’t my cup of tea anyway.”

Sam rolled his eyes and playfully punched Dean on the arm before slurping the last of the pudding from the cup and tossing it in the trash can.

“So you need me to sign a permission slip or something?” Dean asked, happy that at least Sammy would get to have some fun in the absence of their Dad. 

Sam reached into his pocket and pulled out a folded piece of paper, handing it to Dean. He unfolded it and skimmed over the details. It was mostly the typical stuff, like  _ the school is not liable if your kid drowns in the starfish tank _ kind of stuff, but one line caught his eye.  _ There will be a $25 fee for the trip to cover the cost of transportation, lunch, and the aquarium tour. _

“Sammy,” Dean sighed out in anguish, knowing he’d have to crush his little brother’s hopes. “You can’t go on the trip.”

“Why not?” Sam asked, his eyes filling with sadness and confusion.

“Because, Sammy…it’s too much money. We can’t afford it, especially now that Dad isn’t gonna be back for another week. I’m sorry kiddo,” Dean said softly, wishing that Sam was still little so that he could hold him in his lap and comfort him.

Sam’s eyes immediately filled with tears that he tried to blink back, but one snuck out of the corner of his eye and rolled down his cheek, leaving a damp trail in its wake. “So I can’t go? No matter what?” he asked, his voice cracking in disappointment.

Dean swallowed back the sadness he felt in disappointing his little brother and shook his head. “No, you can’t Sammy. I’m sorry.”

Sam wiped his runny nose on his sleeve and angrily wiped the dampness off of his face, attempting to regain his composure. 

“Okay. That’s okay,” he forced out roughly before pushing away from the table and stomping up the stairs to his room.

Dean felt awful. God, why did his dad have to do this all the time? He constantly put Dean in a bind, forcing him to make difficult decisions that a parent should be making. Dean was not a parent, but it still felt like he was constantly being a mother and a father to his little brother, and himself.

He stood from the table and pulled the 40 dollars from his pocket, staring at it thoughtfully _. It’s only money,_ _I mean, it’s not that bad if we run out, right?_ They had bread and eggs left, and Dean was sure there were a couple cans of beans in the cupboard.

God, he was going to regret this. 

“Hey Sammy, I just found 30 bucks in my pocket, so I guess you can go on that field trip after all,” Dean lied, yelling up to his brother. As Sam came down the stairs, practically galloping, Dean took a twenty and a five out of the small pile and shoved the rest in his pocket.

“You honestly mean it?” Sam asked, his eyes practically glowing with hope.

Dean forced on a smile and nodded, and Sam practically tackled him in happiness. “Thanks De,” he said into Dean’s chest, hugging him around the waist. Dean hugged back tightly, kissing the top of Sammy’s head, and the doubt and fear he felt all washed away in knowing how happy he had made his little brother.

=

Later that night, when he knew Sam was asleep, Dean slipped on his boots and carefully snuck out of the house. He shrugged his shoulders into his leather jacket, feeling a slight shiver run through him from the crisp October air. 

He began walking towards town, remembering that he had seen a few bars. Hopefully one of them had a pool table, and hopefully Dean would have a chance at hustling his way into more money.

He took the two remaining bills out of his pocket and his stomach sank. 15 dollars, that’s all that was left. God, he was screwed.

He walked into the busiest looking bar, scoping the scene for pool players. He found a few guys willing to bet, but they all turned Dean down when he told them all he had to bet.

Utterly demoralized and out of options, he slunk towards the bar, plopping himself onto one of the stools. He put his arms on the counter and buried his face in his hands. 

“Can I get you anything?” the bartender asked. Dean looked up briefly and shook his head no, even though he  _ really  _ could use a drink right about now. 

“Hey sweetie, you old enough to be in here?” he heard a female voice ask to his left. He looked up again and didn’t bother answering, just returned his head to it’s pathetic position.

He heard the same voice call for the bartender and say, “get me a couple whiskies.” 

He looked up when he felt her slide the glass over to him, with a look of understanding in her eyes.

He nodded a thanks before knocking the drink down in one gulp, and her eyes widened. “Might wanna slow it down there sweetie,” she said, but motioned to the bartender for a refill.

“Rough day?” she asked, scooting a little closer to Dean.

“You could say that,” he said, pouring the second whiskey down his throat. The woman told the bartender to keep the drinks coming, and Dean felt a little guilty for letting her buy drinks for him, but honestly at this point, he’d rather be drunk and guilty than sober and miserable.

“Wanna talk about it?” she asked, pushing her long black hair behind her shoulders. Her blue eyes were crinkled with something akin to worry, and Dean sighed, feeling like maybe he did want to talk about it.

“I’m just kind of screwed. I’m supposed to be taking care of my little brother, but we completely ran out of money. I’ve only got fifteen bucks left,” Dean said mournfully, draining his glass for the third time.

“Oh, sweetie, that’s tough. How long does it have to last you?” 

“A week.”

She made a noise of pity, gently patting him on the shoulder. “I’m sorry to hear that. Are you boys homeless? There is a homeless shelter not far from here,” she offered, rubbing comforting circles on Dean’s back.

He shook his head. “Not homeless. Just fatherless at the moment,” he mumbled, feeling the alcohol begin to pump through his system.

“I wish I could do more for you sweetie, but there ain’t much I can do. I don’t have much money myself,” she said, looking genuinely regretful.

“I’m sorry, I’ve been letting you buy me drinks, I shouldn’t have,” Dean replied, reaching into his pocket to unwillingly pay her back. She stopped him, gently grabbing his hand.

“Don’t worry about it sweetie, really. I don’t mind at all, I know we’ve all been down in the dumps before. Just remember this the next time you come across someone who’s down on their luck.”

Her sweet smile and generosity warmed Dean’s heart (with a little help from all the whiskey), and he smiled back.

She sat and sipped her drink quietly for a few moments, and that was when Dean noticed the two men eying her from across the bar. They didn’t seem to be together, but they both were looking at her like a piece of meat.

As one of them began walking closer, Dean nudged his companion gently, mumbling “creepy guy at 3 o’clock.”

She casually turned her head, flipping her hair inconspicuously before turning her attention back to Dean. 

“Thanks, dear. It’s been nice meeting you, but I've got to go,” she replied with a wink. Dean was surprised and a little confused, but sat back to watch the scene play out. 

The guy came up and began chatting her up, using some cheesy pick up lines that made Dean roll his eyes, but she began laughing prettily, placing her hands on his chest and flirting back. After a few minutes of small talk, he finally asked the big question: “Do you wanna get out of here?”

“Only if you can afford it, sweetie,” she replied coolly, and Dean’s eyes went wide.  _ She’s a prostitute?  _

“How much?” he asked, unfazed by her comment.

“Hundred an hour, or 500 for the night,” she replied. He checked his wallet and nodded, and they stood up from the bar to leave.

“I hope things get better, sweetie,” she said to Dean earnestly before patting him on the shoulder and leaving the bar with her arms wrapped around that guy.

“Well shit,” Dean mumbled to himself, swigging down his last drink. A prostitute? He never would have guessed. She was so sweet and nice, Dean couldn’t help but wonder what had pushed her into doing such a thing.

Dean sat looking sadly into his empty glass, wishing it were full of amber brown liquid again. He already had a good buzz going, but he really wanted to get drunk enough to stop worrying so much about the 15 dollars in his pocket.

He was lost in thought when he felt another body slide into the unoccupied stool next to him. “I’ll take another round over here,” Dean heard a male voice say, and he looked over in curiosity.

A tall, muscular man with bright brown eyes had seated himself next to Dean, flashing him a beautiful white smile. Dean looked down in confusion when the man slid another whiskey into his hand.

The man laughed when he realized Dean was a little too buzzed to think of anything to say. “Well, you could start by saying thanks,” he joked, his laughter smooth and manly.

“Thanks,” Dean mumbled, taking the drink. He eyed the man nervously, unsure of why he was being so generous. Guessing from the crinkles around his eyes and his slightly graying hair, Dean figured he was probably in his late thirties.

“And next, you could tell me your name,” the man said smoothly, knocking down his own drink.

“It’s Dean,” he responded, before he could remember not to give his real name. 

“Well Dean, I’m James. It’s nice to meet you,” he said, holding out his hand for a handshake. Dean stared at the large, intimidating hand for a moment before shaking it, causing James to let out another laugh.

“You feeling okay?” 

“Jus a little buzzed,” Dean slurred out. Okay, so maybe he was drunker than he thought.

“Well, maybe we should slow down then,” he said, stopping the bartender from filling Dean’s glass again.

Dean just nodded, knowing that getting plastered wasn’t a good idea anyway, considering the fact that he had to walk home.

His brain only registered that James was speaking to him when he felt a heavy hand land on his thigh. When had they even gotten that close to each other?

He looked up and James was only inches away, talking in a low voice.

“Now I would like to know, what is a young guy like you doing in a place like this?” he asked, sliding his hand a little higher up Dean’s leg.

Dean didn’t know what to do. He had never been in a situation like this before, and the alcohol pumping through his system definitely wasn’t helping him figure out how to handle things. 

“I…um…I was looking to play pool. Make some money,” Dean replied, choosing to ignore the man’s advances for now.

“Down on your luck?” James asked, his eyes glinting with something that made Dean a little nervous.

“Uh, yeah. I’ve only got 15 bucks to my name,” Dean said with a humorless laugh, feeling pathetic.

“Oh, I’m sorry to hear that. But you know, I might be able to help out.” James moved his hand even higher, getting dangerously close to Dean’s crotch.

“Yeah?” Dean asked, eying the hand nervously.

“Yeah. How much do you charge an hour?”

The sudden question and the brazenness of the suggestion made Dean’s eyes go wide.

“I don’t- I- I’m not a prostitute,” Dean defended, looking at the man in shock.

James seemed unfazed, even dared to lean in a little closer. “Come on baby, I saw you with your pretty friend earlier, I know a couple of hookers when I see them. I’ve got money, so just tell me, how much?”

Dean’s brain did a back-flip, and he jerked away from the traveling hand and James’s intense gaze. “I meant it, I’m not a prostitute.”

James immediately softened his gaze, looking at Dean with sad eyes. “Really? I’m sorry, I honestly didn’t know.”

Dean said nothing, just turned his attention back to the bar, pretending to be very interested in the shiny finished wood surface. James didn’t leave, he just sat quietly, as if expecting Dean to say something.

_ What in the actual fuck?  _ Dean thought in disbelief.  _ A prostitute? How could he think I was a prostitute?  _ The word played over and over in his head, alongside the image of the measly 15 dollars in his pocket.  _ A prostitute. A fucking prostitute.  _

He reached into his pocket and felt the two small bills, feeling his gut wrench once again. Maybe it was the whiskey in his system, or maybe it was the absolute desperation he felt, but before he knew what he was doing he had turned his attention back to James.

“What would you want me to do?” the words left his mouth before his brain could process it, and he forced himself not to think too much about what he was considering here.

“Anything you’re willing to do, baby. I’ll pay accordingly,” James promised with a smile, returning his hand to Dean’s upper thigh.

Dean looked down at that hand, then up into James’s eyes, and felt something inside of him break a little. Suddenly, he felt incredibly nervous, and it must have shown on his face because James’s smile broke into a look of concern.

“Hey, what’s wrong?” he asked, but Dean offered no answer. Tears had begun welling up in his eyes, but they didn’t spill over.

“Are you a virgin?”

The question hit Dean like a train and he felt the breath leave his lungs. He fervently shook his head no, because even in his drunken state of desperation, he’d be damned if someone thought he was a virgin. “No way, not even close dude,” he replied with a scoff.

“Have you ever been with a man?” James asked, not missing a beat.

Dean felt his face heat up, and he slowly shook his head no, feeling incredibly anxious again.

“Don’t be so nervous,” James said, then leaned in until his lips were right at Dean’s ear. “We should get out of here.”

Before he knew what was happening, Dean was allowing himself to be dragged through the back door of the bar, into the dimly lit alleyway outside. The chilly air hit him in the face and he shivered, thankful for the whiskey warming his blood.

James stood in front of him and Dean looked up into his eyes. His broad shoulders and muscular build overshadowed Dean’s own. “Are you sure you want to do this?”

Dean hesitated, because honestly, no, he didn’t want to do this. At all. But what other choice did he have? He knew John wouldn’t be back for at least a week, but knowing his dad, he could be gone for another 3. He couldn’t stretch 15 dollars out that long and he knew it. Plus, he knew that Sam was getting suspicious that Dean was stressing about something, and since Dean practically told him they were running out of money, he knew Sam could easily deduce that Dean was freaking out about how they were going to have enough money to live until their dad got back. Dean also knew that Sammy would worry himself over it too, and the thought of Sam stressing over something as stupid as money made Dean sure that he had to do this.

He nodded slowly, and James took another step forward, now only inches from Dean. 

“How much do you want, baby?” he asked, and Dean thought a moment.

“Um…two…two fifty?” he decided, looking up into James’s eyes nervously.

“I’ll throw you an extra 50 since it’s your first time,” he replied, pulling his wallet out and showing Dean the money. Dean reached for it but James snapped his wallet shut, chuckling lowly.

“Ah-ah, you only get paid after you provide a service,” he graveled out darkly, before shoving Dean against the frigid brick wall.

Before he could process what was happening, he felt strong hands pinning his arms to the wall and hot lips cover his own. James began kissing him with fervor, biting Dean’s lip in warning when he neglected to open his mouth. Dean immediately opened up, allowing James to kiss him deeply, the whiskey on their breath mingling between them. Dean could feel the rough stubble rubbing against his skin and it burned a little, but he ignored it and did his best to kiss James back.

It was much different from kissing girls, he discovered. Girls were soft, pliant, and responsive. All Dean had to do was nibble on their bottom lip and run his hands down their sides and they were gasping and begging for more.

This was different. Dean had no control. James’s kisses were hungry, filled with lust and promises of things to come that made Dean’s belly flip over and over, and all he could do was allow it to happen and try his best to play along.

At some point, James had begun unbuttoning Dean’s shirt, revealing his skin to the cold night air. When all the buttons were undone he peeled the jacket and shirt off of Dean’s arms, tossing it aside and exposing his pale skin to the dim light in the alleyway.

Dean felt a breeze come by and his skin began to goose up, and he felt his nipples harden responsively. He felt a blush creep onto his cheeks and tried to cross his arms over his chest, but James grabbed his wrists and kept them at his sides.

“You really are beautiful, you know that?” He rasped out, immediately moving to kiss and bite at Dean’s neck, undoubtedly leaving dark hickeys.

Dean was trembling, and he tried to gain control over his body, but it was useless. He continued to quake in James’s grip while he marked up his pale skin, leaving hickey after hickey on Dean’s neck and collar bone.

His hands moved up and he brushed his thumbs over Dean’s nipples, causing him to let out a reactionary gasp. Dean felt his blush deepen and he locked his lips shut, determined not to let out another sound.

“It’s okay baby, I wanna hear you,” James whispered hotly into Dean’s ear, gently pinching his nipples between his fingers. 

Dean let out another gasp, louder than the first, and James smiled against his skin. “That’s more like it,” he mumbled, moving his mouth lower and covering Dean’s chest in hot, wet kisses. He rubbed his stubbly cheek over one of Dean’s sensitive nubs and he practically cried out, flattening his hands on the cold wall behind him. James chuckled and took Dean’s nipple into his mouth, biting softly with his teeth and licking slowly and roughly over it.

He really couldn’t help it at this point, he had never felt something like this before. The hot, wet warmth of James’s mouth against his cold skin made every nerve in him feel electrified, and his body began reacting in ways he had not expected at all. Convincing himself it was just the alcohol in his system, Dean allowed a moan to pass through his lips, earning him a pleasured moan in return from his companion.

James moved back up to Dean’s mouth, and he moved his hand to the waist of his own pants. When Dean heard the unmistakable jingle of a belt being undone, he started to panic. He felt himself tense up and James pulled away, hands still working to undo his fly. “Don’t worry, you can go slow,” he promised, finally pushing his pants and boxers down to rest on his thighs. 

He gently guided Dean onto his knees, using one hand to jerk his cock a few times. Dean’s panic only intensified when he saw the large, daunting erection, now only inches from his face.

He looked up at James and wished that this part would end quickly, silently praying in his head.

“Just relax baby,” James comforted, before gently guiding his erection to Dean’s parted lips.

Dean closed his eyes tightly, but James gently tapped the side of his cheek to get his attention. “I want you to look at me,” he rasped out. Dean hesitantly opened his eyes, locking them with James’s, and that’s when he felt the length move into his mouth.

He felt his eyes watering but struggled to keep them open, fearing that if he didn’t do what James asked, he wouldn’t get paid. He tried his best to relax his throat and allow as much in as possible, but it was too hard, and soon he felt his throat begin to tighten up in reaction.

“Just calm down,” James said softly, moving one hand down to gently massage Dean’s throat. He let out a nervous whimper at the hands around his neck, but he felt his muscles begin to relax as James rubbed and massaged it. Once Dean was able to relax again, James pushed the rest of the way in, forcing Dean to deep throat him.

Dean’s eyes were watering uncontrollably now. He told himself that they weren’t tears, but the shame and fear clawing at him seemed to argue otherwise.

Dean began swallowing and letting out gargled noises on reaction, and James moaned lowly and began thrusting shallowly into Dean’s mouth.

“Fuck, this feels so fucking good. You look so pretty with my cock down your throat,” James practically growled, and Dean felt a few more  _ not _ tears escape his eyes at the words.

He sat and focused on staying relaxed, allowing James to thrust into his mouth over and over again. He had finally managed to blank out and stop thinking, until the feeling of two thick fingers sliding into his mouth alongside James’s cock broke him from his trance.

A new feeling of panic began brewing in the pit of his stomach, because he knew what that meant.

James pulled his dick out of the heated mouth with a groan, replacing It with a third finger, thrusting all three in and out of Dean’s mouth while he sucked and licked as he figured he should.

“Such a good, obedient little slut you are. You could make a career outta this, you know,” James grumbled, and Dean pretended that it didn’t cause more tears to fall from his eyes.

James removed his fingers from Dean’s mouth long enough to lift him to his feet and shove him back against the cold wall. He forced them back in almost immediately with a stern command. “Pull your pants down.”

Dean felt the biggest shiver of panic yet, but quickly moved to undo his buckle and fly, pulling his pants down to rest right above his knees. James ripped his fingers from Dean’s mouth and moved them behind him, leaving a cooling trail of saliva down Dean’s left ass cheek before he slipped in between his crack and began pressing against his hole.

Dean gasped again, eyes going wide. He had never, ever, had anyone else touch him there. It felt foreign, and weird, and he couldn’t help but tense up.

James continued to press his fingertip into Dean’s hole before realizing that he was much too tense and it would be impossible to work his fingers past all of that tight muscle.

He then changed tactics, quickly dropping to his knees in front of Dean. He used his free hand to grasp Dean’s relatively flaccid cock, quickly stroking it into hardness.

Dean felt incredibly embarrassed as he felt his cock swell, but he rationalized that he couldn’t really help how his body reacts to stimulation. However, he wondered why James was even bothering to touch him at all.

Once Dean’s cock was fully hard, James didn’t hesitate to take the length into his mouth, pulling a surprised moan from Dean. He hadn’t expected this at all. He felt a new pool of shame and guilt in his stomach as his body reacted to James’s mouth, moaning and gasping and tingling all over.

While Dean was distracted by the blow job, James began trying to push into Dean’s entrance again, but felt that he was still much too tense.

He pulled his mouth off of Dean’s cock and spun him around, pulling his ass to stick out from the wall.

“You need to calm down, Dean,” he said softly, and Dean felt a wave of nausea rise and fall at the mention of his name. It made this all seem dirtier.

He reached around to wrap his fingers back around Dean’s cock, using his other hand to gently spread Dean’s cheeks enough to fit his face in between.

Dean cried out loudly when he felt a tongue prodding at his hole, and he tried to pull away from the foreign sensation. James let go of Dean’s cock and caught his hips, forcing him to stay in place. He bent Dean over farther, revealing more of his pink entrance. When he pressed with his tongue again, Dean jerked a little, but ultimately he didn’t move.

James began gently prodding, pushing, wiggling against Dean’s tight muscles, and Dean was letting out a string of breathy moans and gasps and whimpers, all of which were only serving to arouse him more.

Dean, on the other hand, felt mortified. He didn’t know why it felt so good, it just did. And he couldn’t help himself from letting out all those girly, embarrassing noises.

James felt Dean’s muscles finally relax, and he pushed his tongue in past the first ring of muscle. Dean cried out again, involuntarily pushing back, wanting more of the feeling James was giving him. James chuckled again, pushing his tongue in farther, working the muscles open slowly.

He began thrusting his tongue in and out of Dean’s hole, and when he felt Dean begin to rhythmically hump back onto his face, he brought his fingers back into the mix.

He pressed one finger into Dean’s hole alongside his tongue, and Dean whimpered at the strange feeling. He had never had anything inside of his body before, and it was the weirdest feeling he thought he’d ever experience.

When Dean’s muscles relaxed enough, James removed his tongue and added a second finger instead, standing up behind Dean once more, shallowly thrusting his fingers in and out, in and out.

When he got to three fingers, Dean began showing signs of discomfort, and James slowed it down once more. He focused on shallow thrusts, being sure to gently spread his fingers and push in as deeply as he could. 

When Dean cried out in something akin to pleasure, James was sure he had hit Dean’s prostate.

_ What the fuck was that?  _ Dean thought when he felt a blinding pleasure rip through his body. James touched something in him and it felt indescribable, and when he hit it again, Dean forgot all about his fear and guilt and began shamelessly pushing back on his fingers.

James leaned forward to rest his lips next to Dean’s ear, breathing hotly against his skin.

“Look at you, practically begging for it. My little whore, my sexy little cockslut,” he hissed out, sending shivers down Dean’s spine that he couldn’t recognize as being good or bad.

James pulled away to rummage through his pockets, and Dean felt disgusted at his own desperation for the new sensations to continue. He stayed quiet, pressing his forehead against the wall while James pulled out a condom and ripped it open.

_ This is it. The point of no return.  _ Dean took in a shaky breath and released it, glancing back to see James rolling the condom over his length and stroking himself a little.

He closed his eyes and braced himself, and jumped a little when he felt James spit down his crack, making him feel dirty and cheap. He forced those feelings away with another deep breath and reminded himself that he had to do this, he  _ had  _ to, for Sammy.  _ Anything for Sammy. _

“Ready?” James asked, pressing his erection to Dean’s hole. Dean felt his heart rate pick up, but he remained calm, and nodded his head.

He let out a cry as James began invading his body, and he couldn’t help the tears of pain that leaked from his eyes. It fucking hurt, way more than he thought it would.

“Shh, it’s okay, I promise it gets better,” James comforted, before thrusting in the rest of the way. Dean let out another cry, mostly of shock this time, and practically slammed his head against the brick wall. James was stilled behind him, and he could feel the heat of his body against his back. He could feel the rise and fall of his chest as he breathed, and the slight pulsating sensation where their bodies were connected. The intimacy of it all made him feel sick and uncomfortable, and even though he knew he wasn’t ready yet, he needed James to move, to fuck, to take without caring. Dean decided that would make him feel much better.

“Move,” he ordered, and James began slowly pressing in and out, gently holding Dean by the hips. It hurt still, but Dean couldn’t take it anymore. He felt like he would explode if James kept moving so fucking slow, so carefully, like he thought Dean would break in half. He was gonna lose it if James kept acting as if he fucking cared about him.

“Faster,” Dean ordered through gritted teeth, and held in a whimper of pain when James picked up the pace. The sound of their skin slapping together was starting to make Dean feel sick, so he focused on the sound of blood rushing in his ears instead.

James pulled Dean back a little, bending him over farther, and began thrusting in again, deeper this time.

“Mmm, baby, you feel so fucking good,” he moaned out, his grip tightening on Dean’s hips. He still continued to be gentle, taking care not to hurt Dean, but Dean wouldn’t have it.

“Harder,” he grumbled, pressing his hands against the wall, feeling the bricks leave stinging indentations in his palms. 

“You sure?” 

“Yes!” 

After Dean snapped his answer, James didn’t question any longer, just began mercilessly pounding away. Dean could feel his skin tearing and he knew he’d probably bleed, but he held back the tears, grit his teeth and took it.

“I want to make you feel good,” James breathed out, switching angles and slamming home harder and faster. On the third thrust, he hit Dean’s prostate, causing him to cry out again, jumping a little at the sensation.

He smirked when it happened and kept that angle, slamming in again and again and again. Dean could feel his body trembling; he could hear his own slutty moans leaving his mouth. He could feel his knees get wobbly and his cock jump at the sudden pleasure. 

“Doesn’t it feel good baby?” James growled lowly, picking up his pace even more. Dean simply nodded, allowing louder and sluttier moans to fall from his lips.

James grabbed Dean’s hair and pulled his head back until his lips were right against Dean’s ear. “I want to hear you say it,” he hissed, slamming in harder.

“It feels good!” Dean was sure he had screamed it, but he really didn’t care at this point.

“What does?” James pressed, pulling Dean’s hair harder.

“You…your cock,” Dean managed to gasp out, even though the words felt strange and foreign leaving his lips.

Dean felt too overwhelmed to be embarrassed by his words. He could tell James was getting close because his rhythm was starting to break, and his breathing was becoming more and more labored.

James released Dean’s hair and allowed his hand to wander down in between Dean’s legs. He grabbed hold of Dean’s cock and began stroking fast, causing Dean’s knees to go wobbly again.

“I want you to come for me, baby,” James breathed out hotly against his ear. Dean felt his body react without his consent, desperately pushing back to meet the thrusts.

“Faster, please, faster,” he heard himself beg.

James complied and sped up his strokes, and Dean’s whole body tensed up as he came with an almost desperate cry, covering the wall in front of him. 

James gave a few more pumps before he was spent, filling the condom with a low groan that seemed to snap Dean back into a state of awareness. 

James pulled out and took the condom off, tying it up and throwing it somewhere in the alleyway. Dean rushed to pull his pants back up, feeling embarrassed once his head was clear. He searched frantically for his shirt and jacket and pulled them on, wanting to cover up as quickly as possible.

Once they both were dressed and relatively put together, James reached into his pocket and pulled out his wallet. 

“Here,” he said, handing Dean a small stack of bills. “I threw in a little extra, just because that was incredible. I’m lucky that I got to be your first.” He counted it, and sure enough, 350 bucks.

The note of admiration in James’s voice made Dean want to cringe, but instead, he forced on a smile and took the money, barely keeping himself from flinching when James placed a light kiss on the top of his head.

“Take care of yourself. Hopefully I'll see you around again sometime,” he said with a wave, before disappearing back into the bar.

Dean tried not to think, tried to stop his brain from processing anything that had just happened, and ran home. He didn’t stop at all, just kept sprinting until he saw the small, dilapidated house come into view. 

He threw the door open and raced to the bathroom, quickly tearing off his clothes and stepping into the shower. He turned the water on extra hot, but all that came out was an ice cold stream that made his skin numb. He didn’t care, he just needed to get clean, and wash away the evidence of anything that had happened tonight. 

He promised himself he would never, ever, not in a million years, do that again.

He scrubbed himself raw and only got out of the shower when he could no longer feel his feet. He knew he was probably going to give himself hypothermia or some shit, but he didn’t care at that point. He stepped out of the shower and stared in the mirror, and was shocked to see how terrified he looked. He forced his reflection to calm down, until his face looked relatively normal. He panicked a little upon seeing the hickeys that were left on his chest, and he quickly put clothes on to hide any other marks before he noticed them. 

He wished more than anything that he had a mom at that moment. He wanted his mom to cuddle up to, to tell him everything was okay, to remind him of how strong and important he was. He wanted his mom to smooth his hair down and hug him close. He wanted to feel safe and comforted.

But he didn’t have a mom. He grew up without his mom, and most of the time, without his dad too. All he had was Sammy. His Sammy, who he would do anything for. The only person he really and truly loved in the world.

He ran upstairs and past his own room, quietly opening the door to Sam’s. He made his way inside and over to the bed, watching as his brother’s breaths came in a perfectly even rhythm. He found it comforting to watch Sam sleep sometimes, because he knew that he was safe. It was one of the only simple things in his life.

Before he could stop himself, he climbed into Sam’s bed, pulling his brother to his chest like he did when they were little. His warmth felt like fire on Dean’s freezing skin, and he pulled the covers up tighter around them, wanting to keep Sam warm. He felt Sam stir and wake up, and he gently started stroking his back.

“Dean? Is that you? Why are you so cold?” Sam’s voice asked, groggy from sleep.

“Sh, it’s okay Sam, go back to sleep. I’m sorry for waking you up,” Dean whispered, willing away the tears that seemed so determined to spill over.

“Is everything okay?” Sam asked, looking up into Dean’s eyes with worry.

“Everything is fine Sammy,” Dean lied, hugging his brother closer. Sam knew everything wasn’t fine, but he didn’t ask again, he just relaxed into Dean’s hold, feeling like he was five years old again. He snuggled up to Dean’s chest and clung onto his shirt so that he could smell Dean’s scent. When he was younger, he couldn’t sleep at night unless he had something of Dean’s to snuggle with, something that smelled like him.

Sam told himself he was cuddling with Dean because that’s what his brother clearly needed at the moment, although part of him knew he was enjoying it too. Everything had gotten so complicated when they started growing up, and he honestly just missed being with his brother.

“I love you Sammy, more than anything,” Dean whispered, feeling a few tears roll down his cheeks and land in Sam’s hair. 

“I love you too, De.”

Sam never did find out why Dean came into his room that night to cuddle him, and why everything  _ wasn’t  _ okay. He didn’t bother to ask, because he knew that Dean needed him to let it go and pretend it never happened. So he did.

For as long as he could.


End file.
